DE3041702A1 - Verfahren zur bekaempfung unerwuenschten pflanzenwuchses mit 2-aryloxy-2-azolylalkancarbonsaeureamiden, diese enthaltende herbizide und verfahren zu ihrer herstellung - Google Patents

Verfahren zur bekaempfung unerwuenschten pflanzenwuchses mit 2-aryloxy-2-azolylalkancarbonsaeureamiden, diese enthaltende herbizide und verfahren zu ihrer herstellung

Info

Publication number: DE3041702A1
Authority: DE; Germany
Prior art keywords: methyl; acid; salts; ethyl; ester
Prior art date: 1980-11-05
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Withdrawn

Application number

DE19803041702

Other languages

German (de)

English (en)

Inventor

Eberhard Dipl.-Chem. Dr. 6700 Ludwigshafen Ammermann

Gerhard Dipl.-Chem. Dr. 6940 Weinheim Hamprecht

Gerd Dipl.-Chem. Dr. 6702 Bad Dürkheim Husslein

Bruno Dipl.-Landw. Dr. 6701 Otterstadt Würzer

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

BASF SE

Original Assignee

BASF SE

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1980-11-05

Filing date

1980-11-05

Publication date

1982-06-09

1980-11-05 Application filed by BASF SE filed Critical BASF SE

1980-11-05 Priority to DE19803041702 priority Critical patent/DE3041702A1/de

1981-09-30 Priority to GR66167A priority patent/GR75011B/el

1981-10-05 Priority to EP81107902A priority patent/EP0051155B1/de

1981-10-05 Priority to DE8181107902T priority patent/DE3168514D1/de

1981-10-05 Priority to AT81107902T priority patent/ATE11412T1/de

1981-10-07 Priority to IL64021A priority patent/IL64021A/xx

1981-10-13 Priority to CA000387801A priority patent/CA1189340A/en

1981-10-30 Priority to JP56173133A priority patent/JPS57108001A/ja

1981-11-04 Priority to AU77084/81A priority patent/AU555446B2/en

1981-11-04 Priority to BR8107152A priority patent/BR8107152A/pt

1981-11-04 Priority to DK488081A priority patent/DK488081A/da

1981-11-04 Priority to ZA817610A priority patent/ZA817610B/xx

1981-11-04 Priority to IE2590/81A priority patent/IE51798B1/en

1982-06-09 Publication of DE3041702A1 publication Critical patent/DE3041702A1/de

1986-12-08 Priority to US06/940,222 priority patent/US4789747A/en

Status Withdrawn legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 14
239000004009 herbicide Substances 0.000 title claims abstract description 10
150000001408 amides Chemical class 0.000 title description 21
230000008635 plant growth Effects 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 16
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 11
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
239000001257 hydrogen Substances 0.000 claims abstract description 9
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims abstract description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
230000008569 process Effects 0.000 claims abstract description 5
125000003342 alkenyl group Chemical group 0.000 claims abstract description 4
125000000304 alkynyl group Chemical group 0.000 claims abstract description 3
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
239000002689 soil Substances 0.000 claims abstract 2
-1 3,5-dimethylphenoxy Chemical group 0.000 claims description 99
239000004480 active ingredient Substances 0.000 claims description 21
230000002363 herbicidal effect Effects 0.000 claims description 15
239000000203 mixture Substances 0.000 claims description 9
238000002360 preparation method Methods 0.000 claims description 9
229910052736 halogen Inorganic materials 0.000 claims description 8
150000002367 halogens Chemical class 0.000 claims description 6
229910052751 metal Inorganic materials 0.000 claims description 6
239000002184 metal Substances 0.000 claims description 6
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 4
239000007788 liquid Substances 0.000 claims 2
239000007787 solid Substances 0.000 claims 2
NOIXNOMHHWGUTG-UHFFFAOYSA-N 2-[[4-[4-pyridin-4-yl-1-(2,2,2-trifluoroethyl)pyrazol-3-yl]phenoxy]methyl]quinoline Chemical compound C=1C=C(OCC=2N=C3C=CC=CC3=CC=2)C=CC=1C1=NN(CC(F)(F)F)C=C1C1=CC=NC=C1 NOIXNOMHHWGUTG-UHFFFAOYSA-N 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 10
230000012010 growth Effects 0.000 abstract description 7
125000000217 alkyl group Chemical group 0.000 abstract description 4
125000003710 aryl alkyl group Chemical group 0.000 abstract 1
150000004696 coordination complex Chemical class 0.000 abstract 1
125000001624 naphthyl group Chemical group 0.000 abstract 1
150000003217 pyrazoles Chemical class 0.000 abstract 1
150000003852 triazoles Chemical class 0.000 abstract 1
150000003839 salts Chemical class 0.000 description 47
150000002148 esters Chemical class 0.000 description 29
241000196324 Embryophyta Species 0.000 description 18
239000002253 acid Substances 0.000 description 16
239000003795 chemical substances by application Substances 0.000 description 9
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 9
238000011282 treatment Methods 0.000 description 9
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
239000004202 carbamide Substances 0.000 description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
239000003921 oil Substances 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
239000004305 biphenyl Substances 0.000 description 5
230000000694 effects Effects 0.000 description 5
150000004702 methyl esters Chemical class 0.000 description 5
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
235000013877 carbamide Nutrition 0.000 description 4
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
230000006378 damage Effects 0.000 description 4
235000019260 propionic acid Nutrition 0.000 description 4
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 4
159000000000 sodium salts Chemical class 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 3
241000209219 Hordeum Species 0.000 description 3
241000520028 Lamium Species 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
150000003931 anilides Chemical class 0.000 description 3
239000003995 emulsifying agent Substances 0.000 description 3
125000004494 ethyl ester group Chemical group 0.000 description 3
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 3
239000000575 pesticide Substances 0.000 description 3
239000000243 solution Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
UVMTZTPUIFOAGM-UHFFFAOYSA-N (3-chlorophenyl)carbamic acid Chemical compound OC(=O)NC1=CC=CC(Cl)=C1 UVMTZTPUIFOAGM-UHFFFAOYSA-N 0.000 description 2
125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
MHNNAWXXUZQSNM-UHFFFAOYSA-N 2-methylbut-1-ene Chemical compound CCC(C)=C MHNNAWXXUZQSNM-UHFFFAOYSA-N 0.000 description 2
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 2
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
241000894006 Bacteria Species 0.000 description 2
244000140786 Brassica hirta Species 0.000 description 2
244000025254 Cannabis sativa Species 0.000 description 2
240000006122 Chenopodium album Species 0.000 description 2
240000008853 Datura stramonium Species 0.000 description 2
244000058871 Echinochloa crus-galli Species 0.000 description 2
241000233866 Fungi Species 0.000 description 2
244000100545 Lolium multiflorum Species 0.000 description 2
241000221026 Mercurialis annua Species 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
241000209504 Poaceae Species 0.000 description 2
244000110797 Polygonum persicaria Species 0.000 description 2
235000004442 Polygonum persicaria Nutrition 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
241000533293 Sesbania emerus Species 0.000 description 2
240000002439 Sorghum halepense Species 0.000 description 2
244000062793 Sorghum vulgare Species 0.000 description 2
241000607479 Yersinia pestis Species 0.000 description 2
239000013543 active substance Substances 0.000 description 2
239000000853 adhesive Substances 0.000 description 2
230000001070 adhesive effect Effects 0.000 description 2
235000012211 aluminium silicate Nutrition 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
239000000969 carrier Substances 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
229940125904 compound 1 Drugs 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
125000004093 cyano group Chemical group *C#N 0.000 description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
238000009472 formulation Methods 0.000 description 2
230000035784 germination Effects 0.000 description 2
239000008187 granular material Substances 0.000 description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
125000005394 methallyl group Chemical group 0.000 description 2
JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 2
QYPPRTNMGCREIM-UHFFFAOYSA-N methylarsonic acid Chemical compound C[As](O)(O)=O QYPPRTNMGCREIM-UHFFFAOYSA-N 0.000 description 2
235000019713 millet Nutrition 0.000 description 2
239000011707 mineral Substances 0.000 description 2
235000010755 mineral Nutrition 0.000 description 2
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
231100001184 nonphytotoxic Toxicity 0.000 description 2
235000016709 nutrition Nutrition 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
239000006072 paste Substances 0.000 description 2
230000003032 phytopathogenic effect Effects 0.000 description 2
229920003023 plastic Polymers 0.000 description 2
239000000843 powder Substances 0.000 description 2
OSFBJERFMQCEQY-UHFFFAOYSA-N propylidene Chemical group [CH]CC OSFBJERFMQCEQY-UHFFFAOYSA-N 0.000 description 2
239000011435 rock Substances 0.000 description 2
239000012266 salt solution Substances 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
241000894007 species Species 0.000 description 2
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
239000000725 suspension Substances 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
239000000080 wetting agent Substances 0.000 description 2
WHOZNOZYMBRCBL-OUKQBFOZSA-N (2E)-2-Tetradecenal Chemical compound CCCCCCCCCCC\C=C\C=O WHOZNOZYMBRCBL-OUKQBFOZSA-N 0.000 description 1
LWULXYSYLOIDQY-UHFFFAOYSA-N (6-tert-butyl-3-methyl-2,4-dinitrophenyl) acetate Chemical compound CC(=O)OC1=C(C(C)(C)C)C=C([N+]([O-])=O)C(C)=C1[N+]([O-])=O LWULXYSYLOIDQY-UHFFFAOYSA-N 0.000 description 1
FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 1
RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 description 1
LMGBDZJLZIPJPZ-UHFFFAOYSA-M 1-methyl-4-phenylpyridin-1-ium;chloride Chemical compound [Cl-].C1=C[N+](C)=CC=C1C1=CC=CC=C1 LMGBDZJLZIPJPZ-UHFFFAOYSA-M 0.000 description 1
UYGUFXUBSNDUFA-UHFFFAOYSA-N 2,3,5,6-tetrachlorobenzoic acid Chemical compound OC(=O)C1=C(Cl)C(Cl)=CC(Cl)=C1Cl UYGUFXUBSNDUFA-UHFFFAOYSA-N 0.000 description 1
XZIDTOHMJBOSOX-UHFFFAOYSA-N 2,3,6-TBA Chemical compound OC(=O)C1=C(Cl)C=CC(Cl)=C1Cl XZIDTOHMJBOSOX-UHFFFAOYSA-N 0.000 description 1
YIVXMZJTEQBPQO-UHFFFAOYSA-N 2,4-DB Chemical compound OC(=O)CCCOC1=CC=C(Cl)C=C1Cl YIVXMZJTEQBPQO-UHFFFAOYSA-N 0.000 description 1
239000002794 2,4-DB Substances 0.000 description 1
239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 1
HXKWSTRRCHTUEC-UHFFFAOYSA-N 2,4-Dichlorophenoxyaceticacid Chemical compound OC(=O)C(Cl)OC1=CC=C(Cl)C=C1 HXKWSTRRCHTUEC-UHFFFAOYSA-N 0.000 description 1
PSOZMUMWCXLRKX-UHFFFAOYSA-N 2,4-dinitro-6-pentan-2-ylphenol Chemical compound CCCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O PSOZMUMWCXLRKX-UHFFFAOYSA-N 0.000 description 1
125000001917 2,4-dinitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1*)[N+]([O-])=O)[N+]([O-])=O 0.000 description 1
YOYAIZYFCNQIRF-UHFFFAOYSA-N 2,6-dichlorobenzonitrile Chemical compound ClC1=CC=CC(Cl)=C1C#N YOYAIZYFCNQIRF-UHFFFAOYSA-N 0.000 description 1
QFUSCYRJMXLNRB-UHFFFAOYSA-N 2,6-dinitroaniline Chemical class NC1=C([N+]([O-])=O)C=CC=C1[N+]([O-])=O QFUSCYRJMXLNRB-UHFFFAOYSA-N 0.000 description 1
KHZYOLUYRMKQDB-UHFFFAOYSA-N 2-(2,4-dichlorophenoxy)-2-(1,2,4-triazol-1-yl)acetamide Chemical compound C1=NC=NN1C(C(=O)N)OC1=CC=C(Cl)C=C1Cl KHZYOLUYRMKQDB-UHFFFAOYSA-N 0.000 description 1
YIGXGYDKDDWZLS-UHFFFAOYSA-N 2-(2-methylphenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=CC=C1C YIGXGYDKDDWZLS-UHFFFAOYSA-N 0.000 description 1
ASRSBXRMOCLKQC-UHFFFAOYSA-N 2-(4-chloro-2-methylphenoxy)-n-methoxyacetamide Chemical compound CONC(=O)COC1=CC=C(Cl)C=C1C ASRSBXRMOCLKQC-UHFFFAOYSA-N 0.000 description 1
WNTGYJSOUMFZEP-UHFFFAOYSA-N 2-(4-chloro-2-methylphenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Cl)C=C1C WNTGYJSOUMFZEP-UHFFFAOYSA-N 0.000 description 1
VTLKOQYZSKCBQX-UHFFFAOYSA-N 2-[(4-fluorophenyl)carbamoyl-methylamino]oxyacetic acid Chemical compound OC(=O)CON(C)C(=O)NC1=CC=C(F)C=C1 VTLKOQYZSKCBQX-UHFFFAOYSA-N 0.000 description 1
OOLBCHYXZDXLDS-UHFFFAOYSA-N 2-[4-(2,4-dichlorophenoxy)phenoxy]propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=CC=C(Cl)C=C1Cl OOLBCHYXZDXLDS-UHFFFAOYSA-N 0.000 description 1
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
WDRGQGLIUAMOOC-UHFFFAOYSA-N 2-benzamidooxyacetic acid Chemical compound OC(=O)CONC(=O)C1=CC=CC=C1 WDRGQGLIUAMOOC-UHFFFAOYSA-N 0.000 description 1
WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 1
QMTFTRRIGOCPAU-UHFFFAOYSA-N 2-ethoxy-3,3,5-trimethyl-2h-1-benzofuran Chemical compound C1=C(C)C=C2C(C)(C)C(OCC)OC2=C1 QMTFTRRIGOCPAU-UHFFFAOYSA-N 0.000 description 1
125000004791 2-fluoroethoxy group Chemical group FCCO* 0.000 description 1
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LLWADFLAOKUBDR-UHFFFAOYSA-N 2-methyl-4-chlorophenoxybutyric acid Chemical compound CC1=CC(Cl)=CC=C1OCCCC(O)=O LLWADFLAOKUBDR-UHFFFAOYSA-N 0.000 description 1
125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
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NZQMQVJXSRMTCJ-UHFFFAOYSA-N 3-Methyl-hexanoic acid Chemical compound CCCC(C)CC(O)=O NZQMQVJXSRMTCJ-UHFFFAOYSA-N 0.000 description 1
DMVLRZKLCLWWOP-UHFFFAOYSA-N 3-amino-2,5,6-trichlorobenzoic acid Chemical compound NC1=CC(Cl)=C(Cl)C(C(O)=O)=C1Cl DMVLRZKLCLWWOP-UHFFFAOYSA-N 0.000 description 1
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JWNBCQQQLMTPLP-UHFFFAOYSA-N 3-propoxypyrrolidine Chemical compound CCCOC1CCNC1 JWNBCQQQLMTPLP-UHFFFAOYSA-N 0.000 description 1
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ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical compound CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 description 1
RHPUJHQBPORFGV-UHFFFAOYSA-N 4-chloro-2-methylphenol Chemical compound CC1=CC(Cl)=CC=C1O RHPUJHQBPORFGV-UHFFFAOYSA-N 0.000 description 1
125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 1
MVXMNHYVCLMLDD-UHFFFAOYSA-N 4-methoxynaphthalene-1-carbaldehyde Chemical compound C1=CC=C2C(OC)=CC=C(C=O)C2=C1 MVXMNHYVCLMLDD-UHFFFAOYSA-N 0.000 description 1
125000004920 4-methyl-2-pentyl group Chemical group CC(CC(C)*)C 0.000 description 1
UZBAJPRDMDYMMI-UHFFFAOYSA-N 5-amino-4-bromo-2-(3-methylphenyl)pyridazin-3-one Chemical compound CC1=CC=CC(N2C(C(Br)=C(N)C=N2)=O)=C1 UZBAJPRDMDYMMI-UHFFFAOYSA-N 0.000 description 1
VLQPYEINHVCCMX-UHFFFAOYSA-N 5-amino-4-chloro-2-cyclohexylpyridazin-3-one Chemical compound O=C1C(Cl)=C(N)C=NN1C1CCCCC1 VLQPYEINHVCCMX-UHFFFAOYSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/16—Halogen atoms or nitro radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Agronomy & Crop Science (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Plural Heterocyclic Compounds (AREA)

DE19803041702 1980-11-05 1980-11-05 Verfahren zur bekaempfung unerwuenschten pflanzenwuchses mit 2-aryloxy-2-azolylalkancarbonsaeureamiden, diese enthaltende herbizide und verfahren zu ihrer herstellung Withdrawn DE3041702A1 (de)

Priority Applications (14)

Application Number	Priority Date	Filing Date	Title
DE19803041702 DE3041702A1 (de)	1980-11-05	1980-11-05	Verfahren zur bekaempfung unerwuenschten pflanzenwuchses mit 2-aryloxy-2-azolylalkancarbonsaeureamiden, diese enthaltende herbizide und verfahren zu ihrer herstellung
GR66167A GR75011B (cs)	1980-11-05	1981-09-30
EP81107902A EP0051155B1 (de)	1980-11-05	1981-10-05	Verwendung von 2-Aryloxy-2-triazolylalkancarbonsäureamiden zur Bekämpfung unerwünschten Pflanzenwuchses und diese enthaltende Herbizide
DE8181107902T DE3168514D1 (en)	1980-11-05	1981-10-05	Use of 2-aryloxy-2-azolylalkanecarbonic amides as herbicides and herbicides containing these amides
AT81107902T ATE11412T1 (de)	1980-11-05	1981-10-05	Verwendung von 2-aryloxy-2triazolylalkancarbons\|ureamiden zur bekaempfung unerwuenschten pflanzenwuchses und diese enthaltende herbizide.
IL64021A IL64021A (en)	1980-11-05	1981-10-07	Herbicidal method and compositions comprising 2-aryl-oxy-2-azolylalkane-carboxamides,their manufacture and certain novel such compounds
CA000387801A CA1189340A (en)	1980-11-05	1981-10-13	Control of unwanted plant growth with 2-aryloxy-2- azolylalkane-carboxamides, herbicides containing them, and the manufacture thereof
JP56173133A JPS57108001A (en)	1980-11-05	1981-10-30	Herbicide containing 2-aryloxy-2-azolylalkane carboxylic acid amide
AU77084/81A AU555446B2 (en)	1980-11-05	1981-11-04	Control unwanted plant growth with i-aryloxy-2 azolylalkane carboxamides
BR8107152A BR8107152A (pt)	1980-11-05	1981-11-04	Composicoes herbicidas baseadas sobre derivados de acido ariloxi-alcano-carboxilico para o combate de vegetacao indesejavel
DK488081A DK488081A (da)	1980-11-05	1981-11-04	Herbicider indeholdende 2-aryloxy2-azolylalkancarboxylsyreamider samt fremgangsmaade til fremstilling heraf
ZA817610A ZA817610B (en)	1980-11-05	1981-11-04	Control of unwanted plant growth with 2-aryloxy-2-azolylalkane-carboxamides,herbicides containing them,and the manufacture theroeof
IE2590/81A IE51798B1 (en)	1980-11-05	1981-11-04	Control of unwanted plant growth with 2-aryloxy-2-triazolyl-alkane-carboxamides,herbicides containing them,and the manufacture thereof
US06/940,222 US4789747A (en)	1980-11-05	1986-12-08	Control of unwanted plant growth with 2-aryloxy-2-azolylalkanecarboxamides, herbicides containing them, and the manufacture thereof

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19803041702 DE3041702A1 (de)	1980-11-05	1980-11-05	Verfahren zur bekaempfung unerwuenschten pflanzenwuchses mit 2-aryloxy-2-azolylalkancarbonsaeureamiden, diese enthaltende herbizide und verfahren zu ihrer herstellung

Publications (1)

Publication Number	Publication Date
DE3041702A1 true DE3041702A1 (de)	1982-06-09

Family

ID=6116004

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
DE19803041702 Withdrawn DE3041702A1 (de)	1980-11-05	1980-11-05	Verfahren zur bekaempfung unerwuenschten pflanzenwuchses mit 2-aryloxy-2-azolylalkancarbonsaeureamiden, diese enthaltende herbizide und verfahren zu ihrer herstellung
DE8181107902T Expired DE3168514D1 (en)	1980-11-05	1981-10-05	Use of 2-aryloxy-2-azolylalkanecarbonic amides as herbicides and herbicides containing these amides

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
DE8181107902T Expired DE3168514D1 (en)	1980-11-05	1981-10-05	Use of 2-aryloxy-2-azolylalkanecarbonic amides as herbicides and herbicides containing these amides

Country Status (13)

Country	Link
US (1)	US4789747A (cs)
EP (1)	EP0051155B1 (cs)
JP (1)	JPS57108001A (cs)
AT (1)	ATE11412T1 (cs)
AU (1)	AU555446B2 (cs)
BR (1)	BR8107152A (cs)
CA (1)	CA1189340A (cs)
DE (2)	DE3041702A1 (cs)
DK (1)	DK488081A (cs)
GR (1)	GR75011B (cs)
IE (1)	IE51798B1 (cs)
IL (1)	IL64021A (cs)
ZA (1)	ZA817610B (cs)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5264415A (en) *	1992-06-25	1993-11-23	Rohm And Haas Company	Fungicidal and herbicidal triazoles
CN1037616C (zh) *	1993-07-15	1998-03-04	中国科学院兰州化学物理研究所	多功能润滑油添加剂

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NZ178996A (en) *	1974-11-15	1978-06-02	Kornis G	Pyrfazole amides and thioamides;herbicidal compositions
DE2720654A1 (de) *	1977-05-07	1978-11-16	Bayer Ag	Azolyl-alkancarbonsaeure-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide
DE2845293A1 (de) *	1978-10-18	1980-05-08	Basf Ag	Alpha -azolyl- alpha -phenylessigsaeurederivate
DE2846127A1 (de) *	1978-10-23	1980-04-30	Basf Ag	1,2,4-triazol-1-yl-verbindungen, ihre hersttellung und verwendung als fungizide
DE2846038A1 (de) *	1978-10-23	1980-05-08	Basf Ag	1,2,4-triazolderivate, ihre herstellung und verwendung
DE2901593A1 (de) *	1979-01-17	1980-08-07	Basf Ag	N-azolylessigsaeureanilide

1980
- 1980-11-05 DE DE19803041702 patent/DE3041702A1/de not_active Withdrawn
1981
- 1981-09-30 GR GR66167A patent/GR75011B/el unknown
- 1981-10-05 EP EP81107902A patent/EP0051155B1/de not_active Expired
- 1981-10-05 AT AT81107902T patent/ATE11412T1/de not_active IP Right Cessation
- 1981-10-05 DE DE8181107902T patent/DE3168514D1/de not_active Expired
- 1981-10-07 IL IL64021A patent/IL64021A/xx unknown
- 1981-10-13 CA CA000387801A patent/CA1189340A/en not_active Expired
- 1981-10-30 JP JP56173133A patent/JPS57108001A/ja active Pending
- 1981-11-04 BR BR8107152A patent/BR8107152A/pt unknown
- 1981-11-04 DK DK488081A patent/DK488081A/da not_active Application Discontinuation
- 1981-11-04 ZA ZA817610A patent/ZA817610B/xx unknown
- 1981-11-04 IE IE2590/81A patent/IE51798B1/en unknown
- 1981-11-04 AU AU77084/81A patent/AU555446B2/en not_active Ceased
1986
- 1986-12-08 US US06/940,222 patent/US4789747A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
ZA817610B (en)	1982-11-24
AU555446B2 (en)	1986-09-25
IL64021A (en)	1986-04-29
IE812590L (en)	1982-05-05
DK488081A (da)	1982-05-06
IE51798B1 (en)	1987-04-01
US4789747A (en)	1988-12-06
JPS57108001A (en)	1982-07-05
DE3168514D1 (en)	1985-03-07
GR75011B (cs)	1984-07-12
IL64021A0 (en)	1982-01-31
CA1189340A (en)	1985-06-25
AU7708481A (en)	1982-05-13
ATE11412T1 (de)	1985-02-15
BR8107152A (pt)	1982-07-20
EP0051155B1 (de)	1985-01-23
EP0051155A1 (de)	1982-05-12

Legal Events

Date	Code	Title	Description
1983-03-03	8130	Withdrawal

Publication	Publication Date	Title
EP0024669B1 (de)	1983-04-06	Substituierte N-Benzoylanthranilsäurederivate und deren Anhydroverbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide und Mittel dafür
EP0060429B1 (de)	1984-01-25	Dichlorchinolinderivate, ihre Herstellung, ihre Verwendung als Herbizide und Mittel dafür
EP0056119B1 (de)	1985-08-07	Substituierte Diphenylether, diese enthaltende Herbizide und ihre Anwendung als Herbizide
EP0071707A1 (de)	1983-02-16	Cyclohexandionderivate, Verfahren zu ihrer Herstellung und diese enthaltende Herbizide
DE3020869A1 (de)	1981-12-17	Aralkylphenylharnstoffe und diese enthaltende herbizide
EP0037925A1 (de)	1981-10-21	Substituierte Pyridazone, Verfahren zu ihrer Herstellung, diese enthaltende Herbizide und ihre Anwendung als Herbizide
EP0032242A1 (de)	1981-07-22	4H-3,1-Benzoxazinderivate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung unerwünschten Pflanzenwuchses
EP0053678A1 (de)	1982-06-16	5-Amino-1-phenyl-4-cyanpyrazole, diese enthaltende herbizide Mittel, Verfahren zu ihrer Herstellung und ihre Anwendung als Herbizide
EP0053698B1 (de)	1985-01-09	5-Amino-1-phenylpyrazol-4-carbonsäureester, Verfahren zu ihrer Herstellung, diese enthaltende Herbizide und ihre Anwendung als Herbizide
EP0046503B1 (de)	1984-06-13	Herbizide Mittel auf der Basis von Cyclohexan-1,3-dion-derivaten und 3,6-Dichlor-2-picolinsäurederivaten
EP0046860B1 (de)	1984-03-14	Cyclohexan-1,3-dion-Derivate
EP0039426B1 (de)	1984-01-18	Thiatriazindioxide und diese enthaltende herbizide Mittel
EP0035712B1 (de)	1983-02-16	N-Aryl(thiol)carbamate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung unerwünschten Pflanzenwuchses
EP0067382B1 (de)	1985-12-04	Chloressigsäurecyclohexylamide, ihre Herstellung, ihre Verwendung zur Bekämpfung von Unkräutern und Mittel dafür
EP0049398A1 (de)	1982-04-14	4H-3,1-Benzoxazinderivate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung unerwünschten Pflanzenwuchses
EP0019171B1 (de)	1982-11-24	Herbizide Mittel auf der Basis von N-Azolylmethyl-halogen-acetaniliden und Cyclohexan-1,3-dionderivaten und ihre Verwendung zur Bekämpfung unerwünschten Pflanzenwuchses
EP0019759B1 (de)	1982-02-10	N-Arylthiolcarbamate, Herbizide, die diese Verbindungen enthalten, und Verfahren zur Bekämpfung unerwünschten Pflanzenwuchses mit diesen Verbindungen
EP0041613B1 (de)	1984-02-01	Aralkylanilinderivate und Herbizide, die diese Verbindungen enthalten
EP0021324B1 (de)	1982-01-20	m-Anilidurethane und diese enthaltende Herbizide
EP0024570B1 (de)	1982-05-12	5-Imino-imidazolin-2-one, diese enthaltende Herbizide und Verfahren zur Bekämpfung unerwünschter Pflanzen mit diesen Verbindungen
EP0019760A1 (de)	1980-12-10	3-Aryl-5-methyl-pyrazol-4-carbonsäureester, diese enthaltende Herbizide, Verfahren zu ihrer Herstellung und ihrer Anwendung
EP0051155A1 (de)	1982-05-12	Verwendung von 2-Aryloxy-2-triazolylalkancarbonsäureamiden zur Bekämpfung unerwünschten Pflanzenwuchses und diese enthaltende Herbizide
EP0025113A1 (de)	1981-03-18	5.6-Dihydro-1.2.4.6-thiatriazin(5)on-1.1-dioxide, Verfahren zu ihrer Herstellung und diese enthaltende Herbizide
EP0044979B1 (de)	1983-11-02	2-Fluoralkancarbonsäureverbindungen, Verfahren zu ihrer Herstellung, diese enthaltende Herbizide und ihre Anwendung
US4515623A (en)	1985-05-07	Control of unwanted plant growth with 2-aryloxy-2-azolylalkanecarboxamides